DK2992334T3 - NEW PHOSPHATIDYL ALKANOLS AND COMPOSITIONS THEREOF - Google Patents

NEW PHOSPHATIDYL ALKANOLS AND COMPOSITIONS THEREOF Download PDF

Info

Publication number: DK2992334T3
Authority: DK; Denmark
Prior art keywords: compound; formula; composition; peth; nmr
Prior art date: 2013-05-03

Application number

DK14791832.0T

Other languages

Danish (da)

English (en)

Inventor

Posaric David Wensbo

Karl-Erik Bergquist

Original Assignee

Pethmark AB

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2013-05-03

Filing date

2014-04-30

Publication date

2018-10-15

2013-05-03 Priority claimed from SE1330045A external-priority patent/SE1330045A1/sv

2014-04-30 Application filed by Pethmark AB filed Critical Pethmark AB

2018-10-15 Application granted granted Critical

2018-10-15 Publication of DK2992334T3 publication Critical patent/DK2992334T3/en

Links

239000000203 mixture Substances 0.000 title claims description 197
150000001875 compounds Chemical class 0.000 claims description 163
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims description 65
239000000654 additive Substances 0.000 claims description 49
125000000217 alkyl group Chemical group 0.000 claims description 42
238000000034 method Methods 0.000 claims description 42
239000002904 solvent Substances 0.000 claims description 40
230000000996 additive effect Effects 0.000 claims description 38
150000003839 salts Chemical class 0.000 claims description 30
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 29
239000002798 polar solvent Substances 0.000 claims description 27
238000005481 NMR spectroscopy Methods 0.000 claims description 26
125000003342 alkenyl group Chemical group 0.000 claims description 25
238000010966 qNMR Methods 0.000 claims description 23
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 claims description 18
HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 claims description 17
238000002360 preparation method Methods 0.000 claims description 16
CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 claims description 15
238000004519 manufacturing process Methods 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
238000005160 1H NMR spectroscopy Methods 0.000 claims description 12
150000003863 ammonium salts Chemical class 0.000 claims description 10
230000015572 biosynthetic process Effects 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
ZMXDDKWLCZADIW-YYWVXINBSA-N N,N-dimethylformamide-d7 Chemical compound [2H]C(=O)N(C([2H])([2H])[2H])C([2H])([2H])[2H] ZMXDDKWLCZADIW-YYWVXINBSA-N 0.000 claims description 9
239000003599 detergent Substances 0.000 claims description 9
238000001914 filtration Methods 0.000 claims description 8
230000010354 integration Effects 0.000 claims description 8
WYURNTSHIVDZCO-SVYQBANQSA-N oxolane-d8 Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])C1([2H])[2H] WYURNTSHIVDZCO-SVYQBANQSA-N 0.000 claims description 7
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
229910052805 deuterium Inorganic materials 0.000 claims description 6
229920001213 Polysorbate 20 Polymers 0.000 claims description 5
238000001514 detection method Methods 0.000 claims description 5
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 claims description 5
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 claims description 5
125000005210 alkyl ammonium group Chemical group 0.000 claims description 4
125000000129 anionic group Chemical group 0.000 claims description 4
125000002091 cationic group Chemical group 0.000 claims description 4
229920002113 octoxynol Polymers 0.000 claims description 4
125000005208 trialkylammonium group Chemical group 0.000 claims description 4
WEVYAHXRMPXWCK-FIBGUPNXSA-N acetonitrile-d3 Chemical compound [2H]C([2H])([2H])C#N WEVYAHXRMPXWCK-FIBGUPNXSA-N 0.000 claims description 3
125000005131 dialkylammonium group Chemical group 0.000 claims description 3
239000000463 material Substances 0.000 claims description 3
150000004671 saturated fatty acids Chemical class 0.000 claims description 3
150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
RYHBNJHYFVUHQT-SVYQBANQSA-N (2H8)-1,4-Dioxane Chemical compound [2H]C1([2H])OC([2H])([2H])C([2H])([2H])OC1([2H])[2H] RYHBNJHYFVUHQT-SVYQBANQSA-N 0.000 claims description 2
ILQZDDQZZVQKLT-UHFFFAOYSA-N 3,4-dihydroxybutan-2-yl dihydrogen phosphate Chemical group P(=O)(O)(O)OC(C(O)CO)C ILQZDDQZZVQKLT-UHFFFAOYSA-N 0.000 claims description 2
XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 2
JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 claims description 2
235000003441 saturated fatty acids Nutrition 0.000 claims description 2
150000005621 tetraalkylammonium salts Chemical group 0.000 claims description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims 2
BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 claims 1
HPNMFZURTQLUMO-UHFFFAOYSA-O diethylammonium Chemical compound CC[NH2+]CC HPNMFZURTQLUMO-UHFFFAOYSA-O 0.000 claims 1
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims 1
QUSNBJAOOMFDIB-UHFFFAOYSA-O ethylaminium Chemical compound CC[NH3+] QUSNBJAOOMFDIB-UHFFFAOYSA-O 0.000 claims 1
ISRXMEYARGEVIU-UHFFFAOYSA-N n-methyl-n-propan-2-ylpropan-2-amine Chemical compound CC(C)N(C)C(C)C ISRXMEYARGEVIU-UHFFFAOYSA-N 0.000 claims 1
ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 claims 1
235000021122 unsaturated fatty acids Nutrition 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 66
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 42
239000000243 solution Substances 0.000 description 35
239000000543 intermediate Substances 0.000 description 32
JCABVIFDXFFRMT-DIPNUNPCSA-N [(2r)-1-[ethoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC)OC(=O)CCCCCCCC=CCCCCCCCC JCABVIFDXFFRMT-DIPNUNPCSA-N 0.000 description 28
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 27
125000004432 carbon atom Chemical group C* 0.000 description 21
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 17
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000011903 deuterated solvents‎ Substances 0.000 description 15
239000000741 silica gel Substances 0.000 description 15
229910002027 silica gel Inorganic materials 0.000 description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 14
-1 PEth Chemical class 0.000 description 13
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
125000003118 aryl group Chemical group 0.000 description 12
125000006239 protecting group Chemical group 0.000 description 12
238000011002 quantification Methods 0.000 description 12
238000004587 chromatography analysis Methods 0.000 description 11
239000007787 solid Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 10
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 description 9
239000003153 chemical reaction reagent Substances 0.000 description 9
238000010908 decantation Methods 0.000 description 9
150000002632 lipids Chemical class 0.000 description 9
230000008901 benefit Effects 0.000 description 8
238000009835 boiling Methods 0.000 description 8
125000001072 heteroaryl group Chemical group 0.000 description 8
238000004895 liquid chromatography mass spectrometry Methods 0.000 description 8
239000012925 reference material Substances 0.000 description 8
241000282414 Homo sapiens Species 0.000 description 7
238000004458 analytical method Methods 0.000 description 7
239000008280 blood Substances 0.000 description 7
210000004369 blood Anatomy 0.000 description 7
238000004821 distillation Methods 0.000 description 7
WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 7
238000003756 stirring Methods 0.000 description 7
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
238000004090 dissolution Methods 0.000 description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
239000003607 modifier Substances 0.000 description 6
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
239000000047 product Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000012088 reference solution Substances 0.000 description 6
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 5
229960000549 4-dimethylaminophenol Drugs 0.000 description 5
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
229910021529 ammonia Inorganic materials 0.000 description 5
239000003963 antioxidant agent Substances 0.000 description 5
229910052799 carbon Inorganic materials 0.000 description 5
239000000356 contaminant Substances 0.000 description 5
229910052739 hydrogen Inorganic materials 0.000 description 5
239000011159 matrix material Substances 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 4
229910019142 PO4 Inorganic materials 0.000 description 4
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
125000004429 atom Chemical group 0.000 description 4
239000000090 biomarker Substances 0.000 description 4
235000010354 butylated hydroxytoluene Nutrition 0.000 description 4
150000001732 carboxylic acid derivatives Chemical group 0.000 description 4
230000008859 change Effects 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
238000000354 decomposition reaction Methods 0.000 description 4
239000003480 eluent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
125000000623 heterocyclic group Chemical group 0.000 description 4
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000003921 oil Substances 0.000 description 4
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 4
239000010452 phosphate Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
239000005642 Oleic acid Substances 0.000 description 3
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
JLPULHDHAOZNQI-JLOPVYAASA-N [(2r)-3-hexadecanoyloxy-2-[(9e,12e)-octadeca-9,12-dienoyl]oxypropyl] 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C\C\C=C\CCCCC JLPULHDHAOZNQI-JLOPVYAASA-N 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
239000006227 byproduct Substances 0.000 description 3
238000006243 chemical reaction Methods 0.000 description 3
229940099352 cholate Drugs 0.000 description 3
239000003086 colorant Substances 0.000 description 3
239000013058 crude material Substances 0.000 description 3
239000002274 desiccant Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000001704 evaporation Methods 0.000 description 3
230000008020 evaporation Effects 0.000 description 3
150000004665 fatty acids Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
150000002430 hydrocarbons Chemical group 0.000 description 3
239000001257 hydrogen Substances 0.000 description 3
230000003301 hydrolyzing effect Effects 0.000 description 3
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
230000001590 oxidative effect Effects 0.000 description 3
239000003002 pH adjusting agent Substances 0.000 description 3
230000026731 phosphorylation Effects 0.000 description 3
238000006366 phosphorylation reaction Methods 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
239000003755 preservative agent Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
159000000000 sodium salts Chemical class 0.000 description 3
239000000126 substance Substances 0.000 description 3
239000006188 syrup Substances 0.000 description 3
235000020357 syrup Nutrition 0.000 description 3
125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 2
MFKMOLJNQHPVHC-SNVBAGLBSA-N (2r)-3-[(4-methoxyphenyl)methoxy]propane-1,2-diol Chemical compound COC1=CC=C(COC[C@H](O)CO)C=C1 MFKMOLJNQHPVHC-SNVBAGLBSA-N 0.000 description 2
YZBOZNXACBQJHI-UHFFFAOYSA-N 1-dichlorophosphoryloxyethane Chemical compound CCOP(Cl)(Cl)=O YZBOZNXACBQJHI-UHFFFAOYSA-N 0.000 description 2
125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 2
208000007848 Alcoholism Diseases 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
OJRUSAPKCPIVBY-KQYNXXCUSA-N C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N Chemical compound C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(CP(=O)(O)O)O)O)O)I)N OJRUSAPKCPIVBY-KQYNXXCUSA-N 0.000 description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 2
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 2
JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
235000021314 Palmitic acid Nutrition 0.000 description 2
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
108090000553 Phospholipase D Proteins 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000000746 allylic group Chemical group 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
239000007864 aqueous solution Substances 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
244000309464 bull Species 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
150000001768 cations Chemical class 0.000 description 2
XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
229940125797 compound 12 Drugs 0.000 description 2
229940125758 compound 15 Drugs 0.000 description 2
239000000470 constituent Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
230000001419 dependent effect Effects 0.000 description 2
230000001066 destructive effect Effects 0.000 description 2
238000011161 development Methods 0.000 description 2
238000009826 distribution Methods 0.000 description 2
230000004590 drinking behavior Effects 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000012634 fragment Substances 0.000 description 2
125000002541 furyl group Chemical group 0.000 description 2
PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
150000002314 glycerols Chemical class 0.000 description 2
230000005484 gravity Effects 0.000 description 2
150000004677 hydrates Chemical class 0.000 description 2
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125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
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APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/10—Phosphatides, e.g. lecithin
- C07F9/106—Adducts, complexes, salts of phosphatides
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B59/00—Introduction of isotopes of elements into organic compounds ; Labelled organic compounds per se
- C07B59/004—Acyclic, carbocyclic or heterocyclic compounds containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur, selenium or tellurium
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/11—Esters of phosphoric acids with hydroxyalkyl compounds without further substituents on alkyl
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N24/00—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects
- G01N24/08—Investigating or analyzing materials by the use of nuclear magnetic resonance, electron paramagnetic resonance or other spin effects by using nuclear magnetic resonance

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Physics & Mathematics (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
High Energy & Nuclear Physics (AREA)
Molecular Biology (AREA)
Analytical Chemistry (AREA)
General Physics & Mathematics (AREA)
Immunology (AREA)
Pathology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other Investigation Or Analysis Of Materials By Electrical Means (AREA)

DK14791832.0T 2013-05-03 2014-04-30 NEW PHOSPHATIDYL ALKANOLS AND COMPOSITIONS THEREOF DK2992334T3 (en)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
SE1330045A SE1330045A1 (sv)	2013-05-03	2013-05-03	Komposition innefattande fosfatidylalkanol för QNMR
SE1430005		2014-01-23
PCT/SE2014/050543 WO2014178787A1 (fr)	2013-05-03	2014-04-30	Nouveaux phosphatidylalcanols et leurs compositions

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DK2992334T3 true DK2992334T3 (en)	2018-10-15

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US (1)	US9499572B2 (fr)
EP (1)	EP2992334B1 (fr)
DK (1)	DK2992334T3 (fr)
ES (1)	ES2688885T3 (fr)
WO (1)	WO2014178787A1 (fr)

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US9784701B2 (en) *	2013-05-03	2017-10-10	Pethmark AB	Phosphatidylalkanols and compositions thereof
ES2938333T3 (es)	2019-01-28	2023-04-10	Redhotdiagnostics Ab	Método para medir una concentración de un biomarcador/analito en sangre de mamíferos
US11813926B2 (en)	2020-08-20	2023-11-14	Denso International America, Inc.	Binding agent and olfaction sensor
US11760169B2 (en)	2020-08-20	2023-09-19	Denso International America, Inc.	Particulate control systems and methods for olfaction sensors
US11881093B2 (en)	2020-08-20	2024-01-23	Denso International America, Inc.	Systems and methods for identifying smoking in vehicles
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US9499572B2 (en)	2016-11-22
US20160052946A1 (en)	2016-02-25
EP2992334A4 (fr)	2017-04-19
EP2992334A1 (fr)	2016-03-09
EP2992334B1 (fr)	2018-06-27
ES2688885T3 (es)	2018-11-07
WO2014178787A1 (fr)	2014-11-06

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